Journal
TETRAHEDRON LETTERS
Volume 53, Issue 37, Pages 4951-4954Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2012.07.006
Keywords
2,1-Benzisoxazole/anthranil; Reduction; Heterocyclization; Stannous chloride; 2-Nitroacylbenzene
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Funding
- University of Maryland School of Pharmacy
- University of Maryland
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Classically, 2,1-benzisoxazoles (anthranils) are prepared from 2-nitroacylbenzenes by a reductive heterocyclization reaction with Sn or SnCl2 concentrated HCl. Acid sensitive functionalities are expected to be incompatible with these conditions; milder approaches to the synthesis of 2,1-benzisoxazoles would be welcomed. We demonstrate that SnCl2 center dot 2H(2)O in a 1:1 mixture of EtOAc/MeOH is capable of mediating the tandem reduction-heterocyclization of a variety of 2-nitroacylbenzenes to their corresponding 2,1-benzisoxazoles in good to excellent yields under essentially neutral conditions. Importantly, several commonly used acid-labile protecting groups, including Boc carbamate, tert-butyl ether, and tert-butyl ester, proved orthogonal to these reaction conditions. (C) 2012 Elsevier Ltd. All rights reserved.
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